EP3752628A1 - Procédé enzymatique permettant de produire des intermédiaires utiles en tant que précurseurs d'esterquat - Google Patents

Procédé enzymatique permettant de produire des intermédiaires utiles en tant que précurseurs d'esterquat

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Publication number
EP3752628A1
EP3752628A1 EP19706116.1A EP19706116A EP3752628A1 EP 3752628 A1 EP3752628 A1 EP 3752628A1 EP 19706116 A EP19706116 A EP 19706116A EP 3752628 A1 EP3752628 A1 EP 3752628A1
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European Patent Office
Prior art keywords
mole
proportion
formula
total
mixture
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
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EP19706116.1A
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German (de)
English (en)
Inventor
Neil Warren Boaz
Jennifer Michelle LLOYD
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Eastman Chemical Co
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Eastman Chemical Co
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Publication of EP3752628A1 publication Critical patent/EP3752628A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/386—Preparations containing enzymes, e.g. protease or amylase
    • C11D3/38627—Preparations containing enzymes, e.g. protease or amylase containing lipase
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2093—Esters; Carbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines

Definitions

  • This invention relates to the field of fabric softeners.
  • it relates to an enzymatic method for preparing intermediates useful in the manufacture of cationic surfactants.
  • Triethanolamine-based ester quaternary ammonium compounds find widespread use as fabric softening agents in rinse-cycle fabric softeners. These materials are generally prepared from triethanolamine and a fatty acid or fatty acid methyl ester using a deficient amount of fatty acid compared to the available number of hydroxyl groups. This deficient but defined amount of fatty acid is used so that a processable ester quat mixture can be obtained, as these water insoluble materials are generally formulated as water-based emulsions. Thus, the acid-catalyzed esterification results in a statistical distribution of esters (mono-, di-, and tri-ester) along with some unreacted triethanolamine that after quaternization can be readily formulated.
  • the deficient amount of fatty acid limits the fatty content of the product, and thus can lead to fabric softening inefficiencies in the balance of competing properties of dispersibility in water versus performance as fabric softening agents.
  • Using higher amounts of fatty acids results in high levels of tri-ester but corresponding low levels of triethanolamine and monoester which makes emulsion formation of the corresponding quat problematic without resorting to additional processing aids.
  • the invention is as set forth in the claims.
  • the invention provides a process for the preparation of a modified
  • the conventional triethanolamine ester composition is a mixture of triethanolamine and esters of the Formulae (II), (III), and (I):
  • each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups.
  • the mole ratio of the four components will depend generally upon the stoichiometry of the reaction in which the mixture is formed but is limited by the statistical nature of the product derived from a non-selective acid catalyst. In conventional processes and resulting mixtures, the stoichiometry is generally in the range of 1.5 to 2 equivalents of fatty acid to triethanolamine.
  • the invention as described herein provides a novel enzymatic process to manufacture a novel triethanolamine/fatty acid ester mixture which is more highly desirable for use in making fabric softeners.
  • the invention provides a method for increasing the molar proportion of triesters of Formula (I)
  • each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups, which comprises contacting said mixture with a hydrolytic enzyme.
  • the method results in increasing the molar proportion of triesters of Formula (I) while decreasing the molar proportion of fatty acid esters of Formula (II) and/or (III).
  • treatment of this triethanolamine/fatty acid ester mixture with an enzyme results in a modification of the ester ratio wherein the combined amount of triethanolamine and monoester is relatively unchanged (3 mol% change or less) but the diester is reduced by at least 4 mol% and the triester is increased by at least 4 mol%.
  • the invention provides a method for increasing the molar proportion of triesters of Formula (I) in a mixture comprising (i) triethanolamine and (ii) fatty acid esters having the Formulae (II), (III) and (I):
  • each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups,
  • the mixture thus produced is a novel consequence of the enzymatic equilibration reaction of the triethanolamine/fatty acid ester mixture; this mixture is particularly desirable insofar as the more desirable triester is increased in relative proportion without materially affecting the monoester (and unesterified material). Accordingly, the process provides a novel mixture of triethanolamine/fatty acid esters which are enhanced in triester concentration, and in other embodiments, also decreased in diester as well.
  • the invention provides a mixture comprising:
  • each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups.
  • the mixtures may be further characterized as having an average Degree of Substitution (DS) of the hydroxyl groups of the triethanolamine and the esters of the Formulae (II), (III), and (I) from about 1.5 to about 1.9.
  • DS Degree of Substitution
  • the invention provides a mixture comprising: a. triethanolamine in a proportion of about 7 to about 15 mole %, based on the total of a, b, c, and d;
  • a fatty acid triester of Formula (I) in a proportion of about 17 to about 27 mole %, based on the total of a, b, c, and d combined, wherein the total mole % of a, b, c, and d equals 100%; wherein each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups.
  • the mixtures may be further characterized as having an average Degree of Substitution (DS) of the hydroxyl groups of the triethanolamine and the esters of the Formulae (II), (III), and (I) from about 1.5 to about 1.75.
  • DS Degree of Substitution
  • novel mixtures referred to above may then be converted to a variety of subsequent materials as is known in the literature for
  • triethanolamine esters Of particular interest is alkylation of the nitrogen to afford cationic surfactants. This alkylation can be performed with dialkyl sulfates such as dimethyl sulfate or diethyl sulfate, benzyl halides such as benzyl chloride, and many others as is known in the art. Cationic surfactants derived from triethanolamine esters find their most widespread utility as hair conditioning agents and particularly as rinse-cycle laundry fabric softeners.
  • RCO is lauroyl, myristoyl, palmitoyl, stearoyl, oleoyl, linoleoyl, or mixtures thereof, or a mixture of C12 to C24 acyl radicals derived from tallow, vegetable, nut, or seed oil.
  • the compounds of formulae (I), (II), and (III) wherein RCO is a mixture are derived from the fatty acids derived from one or more of palm oil, tallow, and partially hydrogenated tallow.
  • hydrocarbyl refers to a mono-valent hydrocarbon group.
  • the term includes groups such as alkyls, alkenes, and alkynes.
  • the hydrocarbyl group R may be substituted or unsubstituted;
  • the hydrocarbyl group R may also be a substituted or unsubstituted C3-C8 cycloalkyl group.
  • R is selected from substituted or unsubstituted, branched- or straight-chain, saturated C5-C19 alkyl; substituted or
  • the hydrocarbyl group of R may be substituted with one to five substituents selected from the group consisting of C1 -C6 alkoxy, C1 -C6 carboxyl, C1 -C15 aminocarbonyl, C1 -C15 amido, cyano, C2-C6 alkoxycarbonyl, C2-C6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C2-C10 dialkylamino, C3-C15 trialkylammonium, chlorine, and bromine.
  • substituents selected from the group consisting of C1 -C6 alkoxy, C1 -C6 carboxyl, C1 -C15 aminocarbonyl, C1 -C15 amido, cyano, C2-C6 alkoxycarbonyl, C2-C6 alkanoyloxy, hydroxy, aryl, heteroaryl, thioether, C2-C10 dialkylamino, C3-C15 trialkylammonium, chlorine,
  • C1-C6 alkoxy As used herein, the terms“C1-C6 alkoxy,”“C2-C6 alkoxycarbonyl,” and “C2-C6 alkanoyloxy” are used to denote radicals corresponding to the structures -OR 2 , -CO2R 2 , and -OCOR 2 , respectively, where R 2 is a substituted or unsubstituted C1-C6 alkyl group.
  • C1 -C15 aminocarbonyl and“C1 -C15 amido” are used to denote radicals corresponding to the structures -NHCOR 3 and - CONHR 3 , respectively, where R 3 is a substituted or unsubstituted C1 -C15 alkyl group.
  • degree of substitution refers to the overall average of the extent of the hydroxyl moieties of the mixture of
  • the maximum DS would be 3.0 as that would represent a fully esterified triethanolamine substrate, whereas a DS of 2 would indicate an average esterification of two of the three hydroxyl groups on the triethanolamine substrate; similarly, when converted to the corresponding quaternary compounds (“quat”), the DS would correspond to the average esterification on the triethanolamine substrate which would remain intact during the alkylation reaction forming the quat.
  • the mixture is prepared by the esterification of triethanolamine with the chosen (but typically substitutionally deficient, i.e., one typically uses less than three full molar equivalents of fatty acid in the reaction to form the esters) amount of fatty acid to afford a mixture of unreacted triethanolamine, monoester (II), diester (III), and triester (I).
  • This reaction can be performed without catalyst (i.e., self-catalyzed) at high temperatures, or, as is known in the art, with a strong acid catalyst.
  • the ratio of products obtained from this esterification is generally a statistical mixture that depends on the ratio of fatty acid to triethanolamine.
  • the method of the invention comprises the enzymatic equilibration of the product mixture from the first step (conventional acid- catalyzed esterification) of the process.
  • the enzymatic equilibration process of the invention may, in certain embodiments, be carried out at a temperature from about -100°C and about +100°C, about 20-90 °C, or about 50-80 °C.
  • the enzymatic equilibration process is performed in the absence of significant amounts of solvent.
  • the solvent can be chosen from cyclic or acyclic ether solvents such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, or tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene, or xylene, aliphatic or alicyclic saturated or unsaturated hydrocarbons such as hexane, heptane,
  • dichloromethane dichloroethane, dibromoethane, tetrachloroethylene, or chlorobenzene
  • polar aprotic solvents such as acetonitrile, dimethyl formamide, or dimethyl sulfoxide, or mixtures thereof.
  • the enzymatic equilibration process uses a hydrolytic enzyme (for example, a protease, lipase, or esterase enzyme); in one embodiment, the enzyme is a lipase.
  • hydrolytic enzyme for example, a protease, lipase, or esterase enzyme
  • the enzyme is a lipase.
  • lipases include but are not limited to Lipase PS (from Pseudomonas sp), Lipase PS-C (from Psuedomonas sp immobilized on ceramic), Lipase PS-D (from Pseudomonas sp immobilized on diatomaceous earth), Lipoprime 50T, Lipozyme TL IM, Novozym® 435 (lipase from Candida antarctica immobilized on acrylic resin), Candida antarctica lipase B immobilized on acrylic resin, or Candida antarctica lipase B
  • Immobilized enzymes such as Lipase PS-C, Lipase PS-D, Novozym® 435, Candida antarctica lipase B immobilized on acrylic resin, or Candida antarctica lipase B immobilized on a porous fluoropolymer support allow simple removal of the product from the insoluble supported enzyme and ready re-use of the enzyme.
  • the pressure of the reaction is generally around atmospheric pressure, but sub- or super-atmospheric pressures can also be used.
  • the enzymatic equilibration process affords a significant change in composition compared to the product ratio obtained by the conventional acid- catalyzed esterification. Examples of this change in composition are shown in Table 2.
  • Table 2 Composition comparison between conventional mixtures and those obtained by the invention for DS 1.6
  • the method of the invention affords at least a 4% decrease in the amount of diester and at least a 5% increase in triester, with the change in some cases being much greater.
  • the upper limit for the change in both the diester and triester is 1 1 mole % in one embodiment and 15 mole% in another embodiment.
  • the product of the second step of the process can be converted to a variety of subsequent materials as is known in the literature for
  • triethanolamine esters Of particular interest is alkylation of the nitrogen to afford cationic surfactants. This alkylation can be performed with dialkyl sulfates such as dimethyl sulfate or diethyl sulfate, benzyl halides such as benzyl chloride, and many others as is known in the art. Cationic surfactants derived from triethanolamine esters find their most widespread utility as hair conditioning agents and particularly as rinse-cycle laundry fabric softeners. See for example, US Patent Nos. 9,476,012, 5,180,508, 9,338,367, and US 2016/0010029, incorporated herein by reference.
  • the invention provides a mixture comprising:
  • each R is independently chosen from straight and branched- chain, saturated and unsaturated C11 -C23 hydrocarbyl groups; wherein R’ is a C1 -C6 alkyl group or a benzyl group and X is chosen from C1 -C6
  • the mixtures may be further characterized as having an average DS of the mixture from about 1.5 to about 1.9.
  • the DS of said mixture is from about 1.5 to about 1.75; a. is present in a proportion of about 7 to about 15%, b. is present in a proportion of about 23 to about 30%, c. is present in a proportion of about 38 to about 45%, and d. is present in a proportion of about 17 to about 27%, based on the total moles of a., b., c., and d., combined, the total equaling 100%.
  • Example 1 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.6 equiv ) without acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification
  • Triethanolamine (15 g; 0.101 mol) was added to tallow fatty acid (Twin Rivers Technology; TRT-1 1 )(43.9 g; 0.176 mol; 1.6 equiv).
  • a 50% water solution of hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equiv) was added and the mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to 70°C.
  • Novozym® 435 (1.40 g) was added to the above mixture at 70°C. The mixture was stirred at 70°C under a nitrogen blanket for 12 hours, and the enzyme was removed by filtration. The composition of the ester after Step 1 and Step 2 is shown below.
  • Example 2 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.5 equiv) without acid catalyst removal
  • Example 3 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.75 equivalents) without acid catalyst removal
  • This example used an identical procedure to Example 1 with triethanolamine (15 g; 0.101 mol), tallow fatty acid (Twin Rivers Technology; TRT-1 1 )(48.0 g; 0.176 mol; 1.75 equiv), 50% hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equiv), and Novozym® 435 (1.50 g).
  • TRT-1 1 tallow fatty acid
  • 50% hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equiv
  • Novozym® 435 (1.50 g.
  • Example 4 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.9 equiv) without acid catalyst removal
  • Example 5 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.75 equiv) without acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification
  • Triethanolamine (15 g; 0.101 mol) was added to tallow fatty acid (Twin Rivers).
  • TRT-1 1 (48.0 g; 0.176 mol; 1.75 equivalents).
  • a 50% water solution of hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equivalents) was added and the mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to 70°C
  • Step 2 Equilibration using lipase from Candida antarctica B immobilized on acrylic resin
  • An immoblized enzyme catalyst (1.50 g) prepared by treatment of the lipase from Candida antarctica B (Novozymes Lipozyme® CalB-L) with an acrylic resin (Lanxess Lewitat® VP OC 1600) was added to the above mixture at
  • Example 6 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.75 equivalents) without acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification
  • Triethanolamine (15 g; 0.101 mol) was added to tallow fatty acid (Twin Rivers Technology; TRT-1 1 )(48.0 g; 0.176 mol; 1.75 equiv).
  • a 50% water solution of hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equiv) was added and the mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to 70°C
  • Step 2 Equilibration using lipase from Candida antarctica B immobilized on fluoropolymer
  • Candida antarctica lipase B (Novozymes Lipozyme® CalB-L) immobilized on a fluoropolymer sheet (270 cm 2 ) cut into small pieces was added to the above mixture at 70°C. The mixture was stirred at 70°C under a nitrogen blanket for 6 hours, and the enzyme was removed by filtration. The composition of the ester after Step 1 and Step 2 is shown below. Table 8
  • Example 7 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.75 equivalents) prepared without acid catalyst
  • Step 1 Conventional non-catalyzed esterification
  • Triethanolamine 324.7 g; 2.18 mol was added to tallow fatty acid (Twin Rivers Technology; TRT-1 1 )(1039.7 g; 3.81 mol; 1.75 equiv). The mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water until the reaction was complete (indicated by an acid number ⁇ 5).
  • Step 2 Equilibration using lipase from Candida antarctica B immobilized on acrylic resin
  • Example 8 Enzymatic equilibration of the ester of triethanolamine with tallow fatty acid (1.75 equivalents) with acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification with acid removal using a basic resin
  • Triethanolamine 324.7 g; 2.18 mol was added to tallow fatty acid (Twin Rivers Technology; TRT-1 1 )(1039.7 g; 3.81 mol; 1.75 equiv). The mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to
  • Step 2 Equilibration using lipase from Candida antarctica B immobilized on acrylic resin
  • the triethanolamine fatty acid ester mixture prepared above was treated with 1.50 g of an immobilized Candida antarctica B lipase (Novozymes Lipozyme® CalB-L) on an acrylic resin (Purolite LifetechTM ECR1030M) at 70°C. The mixture was stirred at 70°C under a nitrogen blanket for 6 hours.
  • the composition of the ester after Step 1 and Step 2 is shown below. Table 10
  • Example 9 Enzymatic equilibration of the ester of triethanolamine with oleic acid (1.75 equivalents) without acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification
  • Triethanolamine (20 g; 0.134 mol) was added to oleic acid (66.3 g; 0.235 mol; 1.75 equiv).
  • a 50% water solution of hypophosphorous acid (0.29 ml_; 0.35 g; 0.002 equiv) was added and the mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to 70°C
  • Novozym® 435 (2.05 g) was added to the above mixture at 70°C. The mixture was stirred at 70°C under a nitrogen blanket for 8 hours, and the enzyme was removed by filtration. The composition of the ester after Step 1 and Step 2 is shown below.
  • Example 10 Enzymatic equilibration of the ester of triethanolamine with palmitic acid (1.75 equivalents) without acid catalyst removal
  • Step 1 Conventional acid-catalyzed esterification
  • Triethanolamine (15 g; 0.101 mol) was added to palmitic acid (45.1 g; 0.176 mol; 1.75 equiv).
  • a 50% water solution of hypophosphorous acid (0.22 ml_; 0.27 g; 0.002 equiv) was added and the mixture was heated with stirring to 140°C with a headspace nitrogen purge to remove the generated water. After 12h the reaction was complete and was cooled to 70°C
  • Novozym® 435 (1.42 g) was added to the above mixture at 70°C. The mixture was stirred at 70°C under a nitrogen blanket for 6 hours, and the enzyme was removed by filtration. The composition of the ester after Step 1 and Step 2 is shown below.
  • This table illustrates the relative compositions of two embodiments of the novel mixtures of the invention.
  • Example 11 Synthesis of N-methyl (triethanolammonium tallow fatty acid ester) methosulfate (TEA ester guat) from enzyme-equilibrated ester of triethanolamine with tallow fatty acid (1.5 equivalents)
  • TEA ester guat N-methyl (triethanolammonium tallow fatty acid ester) methosulfate
  • Dimethyl sulfate (26.55g, 0.2105 mol) was added dropwise into the TEA ester mixture at a rate such that the internal temperature did not exceed 60 °C. After completion of the addition, the mixture was maintained at 60 °C for 7.5 hours at which time all of the dimethyl sulfate was consumed as indicated by 1 H NMR analysis. Free amine titration showed 98% of the TEA ester had been quaternized. The final product contained 90% of N-methyl (triethanolammonium tallow fatty acid ester) methosulfate (TEA ester quat) and 10% I PA.

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Abstract

L'invention concerne un procédé de préparation d'un rapport de composition d'ester d'acide gras/triéthanolamine modifié par traitement d'une composition d'ester d'acide gras/triéthanolamine classique avec une enzyme hydrolytique. L'invention concerne également de nouveaux mélanges de triéthanolamine et de mono-, di-, et tri-esters d'acides gras qui sont utiles à la préparation de tensioactifs cationiques servant dans des applications d'assouplissement du linge. Selon un aspect, le procédé augmente la fraction du tri-ester sans affecter de manière significative la quantité de mono-ester et d'espèces non estérifiées, ce qui à son tour accroît la flexibilité lors de la formulation des compositions d'assouplissement du linge correspondantes.
EP19706116.1A 2018-02-13 2019-02-05 Procédé enzymatique permettant de produire des intermédiaires utiles en tant que précurseurs d'esterquat Pending EP3752628A1 (fr)

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PCT/US2019/016571 WO2019160705A1 (fr) 2018-02-13 2019-02-05 Procédé enzymatique permettant de produire des intermédiaires utiles en tant que précurseurs d'esterquat

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